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Pineapple Upside-Down Cupcakes Recipe

A Classic Tropical Dessert Reimagined as Perfectly Portioned Cupcakes


Introduction: A Beloved Classic in Cupcake Form

Few desserts capture nostalgia and sunshine quite like pineapple upside-down cake. With its caramelized pineapple, buttery brown sugar topping, and moist vanilla cake, it has been a timeless favorite for generations. Now imagine all that flavor transformed into individual cupcakes—easy to serve, beautifully presented, and irresistibly delicious.

These Pineapple Upside-Down Cupcakes are the perfect blend of retro charm and modern convenience. Each cupcake features a glossy caramelized pineapple ring (or chunk), a hint of maraschino cherry, and a tender, fluffy crumb that soaks up the tropical juices. Whether you’re baking for a party, a holiday table, or just to treat yourself, this recipe delivers bakery-style results with home-kitchen simplicity.

This article walks you through everything: ingredients, step-by-step instructions, baking science tips, storage advice, variations, and SEO-friendly serving ideas—so you can confidently master this dessert.


Why You’ll Love These Pineapple Upside-Down Cupcakes

  • Perfect portions – no slicing required

  • Visually stunning – caramelized pineapple on top

  • Moist and tender thanks to pineapple juice and butter

  • Crowd-pleasing flavor with sweet-tangy balance

  • Great make-ahead dessert for parties and events


Ingredients Breakdown

For the Pineapple Topping

  • ½ cup unsalted butter, melted

  • ¾ cup light brown sugar, packed

  • Pineapple slices or chunks (fresh or canned, drained well)

  • Maraschino cherries, halved or whole (optional but classic)

For the Cupcake Batter

  • 1½ cups all-purpose flour

  • 1½ teaspoons baking powder

  • ¼ teaspoon salt

  • ½ cup unsalted butter, softened

  • ¾ cup granulated sugar

  • 2 large eggs, room temperature

  • 1 teaspoon vanilla extract

  • ½ cup pineapple juice (from the can or fresh)

  • ¼ cup milk (whole milk preferred)


Equipment You’ll Need

  • Standard 12-cup muffin pan

  • Paper liners or well-greased pan

  • Mixing bowls (large and medium)

  • Whisk and electric mixer

  • Measuring cups and spoons

  • Cooling rack


Step-by-Step Instructions

Step 1: Preheat and Prepare

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